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United States Patent | 5,350,845 |
Brown, Jr. | September 27, 1994 |
A process for the conversion of a 4-chlorosulfonyl azetidinone (a) to a 3-hydroxy-3-cephem-sulfoxide ester (d) by subjecting an intermediate comprising a tin containing Lewis acid-type Fiedel-Crafts catalyst and 3-exomethylene cepham to ozonolysis.
Inventors: | Brown, Jr.; Frank (West Lafayette, IN) |
Assignee: | Eli Lilly and Company (Indianapolis, IN) |
Appl. No.: | 976592 |
Filed: | November 13, 1992 |
Current U.S. Class: | 540/215; 540/221; 540/222 |
Intern'l Class: | C07D 501/04 |
Field of Search: | 540/215,222,221,228 |
3917587 | Nov., 1975 | Chauvette | 260/243. |
4031084 | Jun., 1977 | Kukolja et al. | 260/243. |
4052387 | Oct., 1977 | Kukolja | 544/22. |
4075203 | Feb., 1978 | Chou | 544/18. |
4081440 | Mar., 1978 | Kukolja | 260/239. |
4115643 | Sep., 1978 | Kukolja et al. | 544/16. |
4190724 | Feb., 1980 | Chou | 544/16. |
4289695 | Sep., 1981 | Chou | 260/239. |
4950753 | Aug., 1990 | Copp et al. | 540/230. |
Journal of Medicinal Chemistry, Chemistry of Cephalosporin Antibiotics. 30 3-Methoxy-and 3-Halo-3-cephems; Chauvette and Pennington vol. 18 No. 4 pp. 403-408 (1975). J. Org. Chem., Kukolja et al.; Synthesis of 3-Hydroxy-, 3-Chloro-, and 3-Methoxy-3-cephems from Penicillins via 4-Dithio-2-azetidinone Intermediates vol. 41 pp. 2276-2278 (1976). Chem. Pharm. Bull., No. 2; Synthesis of 7.beta.-[(Z)-2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-c arboxylic Acid (Ceftizoxime), a New Semisynthetic Cephalosporin Antibiotic. Kobayashi et al. vol. 36 pp. 582-590 (1988). |